Evaluating the role of technology and separating places where technology is the business from ones where it’s an expense:
- How does the company describe the purpose of the technology team?
- Who does the technology team report to? Is it a CTO or a CIO? Who does that person report to: is it a CEO or a CFO?
- How is the technical organization described? You can learn a lot just through the use of terms like engineering vs. “IT,” or R&D vs. “cost center.”
- How do other technology and product functions relate to the technology organization, for example: where do designers report, where do PMs fit?
- What are executives’ biggest concerns with the technology organization? Is it that they can’t hire great people fast enough or that it costs too much?
- How do they describe their unique strategic advantage? Do they talk about engineering innovation as a differentiator, or a commodity and a means to an end?
- Are engineers and technologists involved in the interview process for PMs? If not, that’s a bad sign. If so, ask them if they feel empowered?
- Has the company been able to recruit people from other successful product companies?
- Are there technology leaders on the board of directors?
Identifying capable product leadership and separating them from companies where product leadership is weak or non-existent:
- Who does the product team report to? Is there a senior product leader who reports directly to the CEO or is the PM team subservient to a function like IT or Marketing?
- Does the company have a strong track record of promoting product leaders into general management or even CEO? Are there any product leaders on the board of directors?
- What are the characteristics that are valued in product leaders? Are they seen as innovators or merely doers?
- Who owns the product roadmap? Is it a command-and-control function of sales or general management, or does the product leadership own this?
- Are product leaders considered amongst the most powerful executives at the company?
- During the interview process are you getting to spend enough time with product leaders?
- When asked about the product vision do they share an inspiring customer-focused north star or a tactical set of features and efforts?
Finding empowered product teams (as opposed to feature teams):
- When asked, how does the company describe a “product team”? Who’s included in it?
- Where do projects and initiatives come from? Are they mandated from above or elsewhere in the corporation, or do they emerge from the product teams themselves? A solid question for PMs: “who decides what your team works on next?”
- When asked to describe the role of product management, does it sound more like a tactical project manager or factory floor supervisor?
- Is there a track record of PMs growing in the organization and taking on executive leadership roles?
- How is success measured for a product? Who decides the success criteria? Who measures it?
- Who is responsible for interfacing with users and customers and synthesizing what is learned?
- What is the charter for how product teams are organized: it is around problems to solve or customer needs, or is it particular product surfaces, feature queues, or sales constituents?